NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	3.395
LogD:	3.025
LogS:	-4.155
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.761
Synthetic Accessibility Score:	3.936
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.722
MDCK Permeability:	2.6982119379681535e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	91.89384460449219%
Volume Distribution (VD):	1.205
Pgp-substrate:	10.789971351623535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.243
CYP1A2-substrate:	0.781
CYP2C19-inhibitor:	0.096
CYP2C19-substrate:	0.614
CYP2C9-inhibitor:	0.241
CYP2C9-substrate:	0.74
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	12.263
Half-life (T1/2):	0.651

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.22
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.286
Skin Sensitization:	0.239
Carcinogencity:	0.951
Eye Corrosion:	0.097
Eye Irritation:	0.348
Respiratory Toxicity:	0.972

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC150646

Natural Product ID:	NPC150646
*Common Name:**	7-Ketoisodrimenin-5-Ene
IUPAC Name:	(9aS)-6,6,9a-trimethyl-3,7,8,9-tetrahydrobenzo[g][2]benzofuran-1,4-dione
Synonyms:
Standard InCHIKey:	RJNTWOQXGPYTEQ-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-14(2)5-4-6-15(3)11(14)7-10(16)9-8-18-13(17)12(9)15/h7H,4-6,8H2,1-3H3/t15-/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)C1=CC(=O)C1=C2C(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457166
PubChem CID:	13005952
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33499	porella cordeana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350093]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	1000.0	ug ml-1	PMID[530554]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC150646 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1283
0.2-0.3	5536
0.3-0.4	12816
0.4-0.5	11765
0.5-0.6	6889
0.6-0.7	3646
0.7-0.8	543
0.8-0.85	29
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC282293
0.8765	High Similarity	NPC189311
0.8701	High Similarity	NPC316500
0.859	High Similarity	NPC471220
0.8519	High Similarity	NPC193198
0.8471	Intermediate Similarity	NPC51486
0.8471	Intermediate Similarity	NPC8062
0.8415	Intermediate Similarity	NPC30486
0.8395	Intermediate Similarity	NPC200513
0.8353	Intermediate Similarity	NPC280833
0.8353	Intermediate Similarity	NPC5509
0.8333	Intermediate Similarity	NPC27205
0.8313	Intermediate Similarity	NPC177932
0.8293	Intermediate Similarity	NPC22611
0.8276	Intermediate Similarity	NPC115021
0.8235	Intermediate Similarity	NPC226863
0.8193	Intermediate Similarity	NPC475100
0.8193	Intermediate Similarity	NPC149869
0.8182	Intermediate Similarity	NPC84893
0.8171	Intermediate Similarity	NPC178676
0.8161	Intermediate Similarity	NPC472814
0.8161	Intermediate Similarity	NPC177037
0.8148	Intermediate Similarity	NPC195424
0.8101	Intermediate Similarity	NPC40353
0.8095	Intermediate Similarity	NPC65661
0.8095	Intermediate Similarity	NPC86316
0.8095	Intermediate Similarity	NPC106416
0.8095	Intermediate Similarity	NPC110405
0.809	Intermediate Similarity	NPC209355
0.8049	Intermediate Similarity	NPC475665
0.8025	Intermediate Similarity	NPC471299
0.8023	Intermediate Similarity	NPC472302
0.8023	Intermediate Similarity	NPC215831
0.8	Intermediate Similarity	NPC220478
0.7978	Intermediate Similarity	NPC470697
0.7976	Intermediate Similarity	NPC71626
0.7952	Intermediate Similarity	NPC186276
0.7952	Intermediate Similarity	NPC268122
0.7935	Intermediate Similarity	NPC54705
0.7931	Intermediate Similarity	NPC73995
0.7931	Intermediate Similarity	NPC284561
0.7907	Intermediate Similarity	NPC312561
0.7889	Intermediate Similarity	NPC295347
0.7875	Intermediate Similarity	NPC473223
0.7867	Intermediate Similarity	NPC116013
0.7865	Intermediate Similarity	NPC475657
0.7857	Intermediate Similarity	NPC118423
0.7841	Intermediate Similarity	NPC469595
0.7841	Intermediate Similarity	NPC161638
0.7841	Intermediate Similarity	NPC212679
0.7841	Intermediate Similarity	NPC220454
0.7841	Intermediate Similarity	NPC152467
0.7821	Intermediate Similarity	NPC257618
0.7802	Intermediate Similarity	NPC242848
0.7791	Intermediate Similarity	NPC474062
0.7778	Intermediate Similarity	NPC189206
0.7778	Intermediate Similarity	NPC54996
0.7778	Intermediate Similarity	NPC148463
0.7778	Intermediate Similarity	NPC41780
0.7778	Intermediate Similarity	NPC187568
0.7778	Intermediate Similarity	NPC53685
0.7778	Intermediate Similarity	NPC472300
0.7778	Intermediate Similarity	NPC474555
0.7765	Intermediate Similarity	NPC474359
0.7753	Intermediate Similarity	NPC472953
0.775	Intermediate Similarity	NPC65650
0.7742	Intermediate Similarity	NPC117685
0.7742	Intermediate Similarity	NPC474012
0.7742	Intermediate Similarity	NPC476299
0.7738	Intermediate Similarity	NPC94200
0.7727	Intermediate Similarity	NPC251528
0.7727	Intermediate Similarity	NPC174342
0.7727	Intermediate Similarity	NPC168131
0.7727	Intermediate Similarity	NPC173042
0.7717	Intermediate Similarity	NPC84335
0.7717	Intermediate Similarity	NPC53844
0.7717	Intermediate Similarity	NPC475709
0.7717	Intermediate Similarity	NPC208094
0.7717	Intermediate Similarity	NPC38530
0.7717	Intermediate Similarity	NPC2049
0.7711	Intermediate Similarity	NPC47747
0.7711	Intermediate Similarity	NPC268827
0.7701	Intermediate Similarity	NPC171722
0.7701	Intermediate Similarity	NPC477228
0.7683	Intermediate Similarity	NPC128276
0.7683	Intermediate Similarity	NPC299235
0.7683	Intermediate Similarity	NPC35574
0.7683	Intermediate Similarity	NPC184737
0.7674	Intermediate Similarity	NPC21471
0.7674	Intermediate Similarity	NPC476678
0.7674	Intermediate Similarity	NPC323765
0.7674	Intermediate Similarity	NPC33570
0.7667	Intermediate Similarity	NPC476598
0.7667	Intermediate Similarity	NPC476597
0.7667	Intermediate Similarity	NPC271652
0.7667	Intermediate Similarity	NPC139692
0.7647	Intermediate Similarity	NPC215294
0.764	Intermediate Similarity	NPC469372
0.764	Intermediate Similarity	NPC471818
0.764	Intermediate Similarity	NPC281942
0.764	Intermediate Similarity	NPC477782
0.764	Intermediate Similarity	NPC232426
0.7625	Intermediate Similarity	NPC20025
0.7619	Intermediate Similarity	NPC40228
0.7619	Intermediate Similarity	NPC229584
0.7619	Intermediate Similarity	NPC14203
0.7614	Intermediate Similarity	NPC477128
0.7609	Intermediate Similarity	NPC240673
0.7609	Intermediate Similarity	NPC17578
0.759	Intermediate Similarity	NPC469690
0.7586	Intermediate Similarity	NPC168248
0.7586	Intermediate Similarity	NPC195640
0.7586	Intermediate Similarity	NPC261721
0.7582	Intermediate Similarity	NPC477130
0.7582	Intermediate Similarity	NPC477129
0.7582	Intermediate Similarity	NPC476596
0.7582	Intermediate Similarity	NPC38830
0.7582	Intermediate Similarity	NPC476415
0.7561	Intermediate Similarity	NPC65603
0.7561	Intermediate Similarity	NPC57744
0.7561	Intermediate Similarity	NPC97377
0.7558	Intermediate Similarity	NPC31086
0.7558	Intermediate Similarity	NPC60951
0.7556	Intermediate Similarity	NPC473944
0.7556	Intermediate Similarity	NPC477783
0.7556	Intermediate Similarity	NPC65513
0.7556	Intermediate Similarity	NPC166110
0.7556	Intermediate Similarity	NPC472705
0.7556	Intermediate Similarity	NPC141831
0.7553	Intermediate Similarity	NPC472644
0.7531	Intermediate Similarity	NPC228978
0.7529	Intermediate Similarity	NPC475690
0.7529	Intermediate Similarity	NPC471218
0.7528	Intermediate Similarity	NPC95364
0.7528	Intermediate Similarity	NPC285982
0.7528	Intermediate Similarity	NPC142159
0.75	Intermediate Similarity	NPC478144
0.75	Intermediate Similarity	NPC475678
0.75	Intermediate Similarity	NPC247586
0.75	Intermediate Similarity	NPC183012
0.75	Intermediate Similarity	NPC474956
0.75	Intermediate Similarity	NPC478145
0.7474	Intermediate Similarity	NPC472643
0.7474	Intermediate Similarity	NPC476888
0.7474	Intermediate Similarity	NPC475099
0.7474	Intermediate Similarity	NPC93744
0.7473	Intermediate Similarity	NPC248193
0.7473	Intermediate Similarity	NPC472303
0.7473	Intermediate Similarity	NPC166346
0.7471	Intermediate Similarity	NPC30984
0.7471	Intermediate Similarity	NPC52628
0.7471	Intermediate Similarity	NPC472442
0.7471	Intermediate Similarity	NPC474860
0.7471	Intermediate Similarity	NPC471300
0.747	Intermediate Similarity	NPC253749
0.7447	Intermediate Similarity	NPC316598
0.7444	Intermediate Similarity	NPC159748
0.7444	Intermediate Similarity	NPC101651
0.7444	Intermediate Similarity	NPC158488
0.7444	Intermediate Similarity	NPC476437
0.7444	Intermediate Similarity	NPC476369
0.7442	Intermediate Similarity	NPC470047
0.7442	Intermediate Similarity	NPC477124
0.7442	Intermediate Similarity	NPC12283
0.7442	Intermediate Similarity	NPC475947
0.7442	Intermediate Similarity	NPC311070
0.7442	Intermediate Similarity	NPC222358
0.7442	Intermediate Similarity	NPC472440
0.7442	Intermediate Similarity	NPC470046
0.7442	Intermediate Similarity	NPC474193
0.7439	Intermediate Similarity	NPC263582
0.7439	Intermediate Similarity	NPC41017
0.7439	Intermediate Similarity	NPC235906
0.7436	Intermediate Similarity	NPC218477
0.7419	Intermediate Similarity	NPC112654
0.7419	Intermediate Similarity	NPC29952
0.7419	Intermediate Similarity	NPC476797
0.7419	Intermediate Similarity	NPC234993
0.7419	Intermediate Similarity	NPC134072
0.7416	Intermediate Similarity	NPC471047
0.7416	Intermediate Similarity	NPC469653
0.7416	Intermediate Similarity	NPC475906
0.7416	Intermediate Similarity	NPC24816
0.7416	Intermediate Similarity	NPC196407
0.7416	Intermediate Similarity	NPC469631
0.7416	Intermediate Similarity	NPC469628
0.7412	Intermediate Similarity	NPC471325
0.7412	Intermediate Similarity	NPC474955
0.7412	Intermediate Similarity	NPC275507
0.7412	Intermediate Similarity	NPC42470
0.7396	Intermediate Similarity	NPC40918
0.7396	Intermediate Similarity	NPC476890
0.7391	Intermediate Similarity	NPC475572
0.7391	Intermediate Similarity	NPC474554
0.7386	Intermediate Similarity	NPC470050
0.7386	Intermediate Similarity	NPC470051
0.7386	Intermediate Similarity	NPC279859
0.7386	Intermediate Similarity	NPC471219
0.7386	Intermediate Similarity	NPC474045
0.7386	Intermediate Similarity	NPC194417

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC150646 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1616
0.2-0.3	3994
0.3-0.4	2277
0.4-0.5	725
0.5-0.6	266
0.6-0.7	95
0.7-0.8	10
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8395	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD1694	Approved
0.7586	Intermediate Similarity	NPD6409	Approved
0.7586	Intermediate Similarity	NPD6684	Approved
0.7586	Intermediate Similarity	NPD5330	Approved
0.7586	Intermediate Similarity	NPD7521	Approved
0.7586	Intermediate Similarity	NPD7334	Approved
0.7586	Intermediate Similarity	NPD7146	Approved
0.7531	Intermediate Similarity	NPD8039	Approved
0.7416	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6672	Approved
0.7416	Intermediate Similarity	NPD6903	Approved
0.7416	Intermediate Similarity	NPD5737	Approved
0.7363	Intermediate Similarity	NPD5693	Phase 1
0.7126	Intermediate Similarity	NPD5209	Approved
0.7033	Intermediate Similarity	NPD5208	Approved
0.6957	Remote Similarity	NPD6673	Approved
0.6957	Remote Similarity	NPD6904	Approved
0.6957	Remote Similarity	NPD6080	Approved
0.6947	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5695	Phase 3
0.6923	Remote Similarity	NPD3573	Approved
0.6907	Remote Similarity	NPD4225	Approved
0.6882	Remote Similarity	NPD5207	Approved
0.6882	Remote Similarity	NPD5785	Approved
0.6882	Remote Similarity	NPD5692	Phase 3
0.6842	Remote Similarity	NPD7748	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7900	Approved
0.6835	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6098	Approved
0.6809	Remote Similarity	NPD5694	Approved
0.6809	Remote Similarity	NPD6050	Approved
0.6804	Remote Similarity	NPD6084	Phase 2
0.6804	Remote Similarity	NPD6083	Phase 2
0.6778	Remote Similarity	NPD3133	Approved
0.6778	Remote Similarity	NPD3665	Phase 1
0.6778	Remote Similarity	NPD3666	Approved
0.6771	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6399	Phase 3
0.6735	Remote Similarity	NPD5696	Approved
0.6735	Remote Similarity	NPD7638	Approved
0.6699	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6633	Remote Similarity	NPD7902	Approved
0.6632	Remote Similarity	NPD7515	Phase 2
0.663	Remote Similarity	NPD3618	Phase 1
0.663	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5279	Phase 3
0.663	Remote Similarity	NPD4623	Approved
0.663	Remote Similarity	NPD4519	Discontinued
0.6602	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5654	Approved
0.6596	Remote Similarity	NPD6051	Approved
0.6593	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3667	Approved
0.6556	Remote Similarity	NPD4221	Approved
0.6556	Remote Similarity	NPD4223	Phase 3
0.6517	Remote Similarity	NPD4695	Discontinued
0.6506	Remote Similarity	NPD4137	Phase 3
0.65	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3617	Approved
0.6476	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5959	Approved
0.6458	Remote Similarity	NPD5281	Approved
0.6458	Remote Similarity	NPD5284	Approved
0.6458	Remote Similarity	NPD6411	Approved
0.6429	Remote Similarity	NPD4747	Approved
0.6429	Remote Similarity	NPD4691	Approved
0.6421	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5328	Approved
0.6421	Remote Similarity	NPD4753	Phase 2
0.6415	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3668	Phase 3
0.6413	Remote Similarity	NPD4786	Approved
0.6413	Remote Similarity	NPD4197	Approved
0.6392	Remote Similarity	NPD5779	Approved
0.6392	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD7732	Phase 3
0.6354	Remote Similarity	NPD6698	Approved
0.6354	Remote Similarity	NPD46	Approved
0.6353	Remote Similarity	NPD5276	Approved
0.6346	Remote Similarity	NPD5739	Approved
0.6346	Remote Similarity	NPD7128	Approved
0.6346	Remote Similarity	NPD6008	Approved
0.6346	Remote Similarity	NPD6402	Approved
0.6346	Remote Similarity	NPD6675	Approved
0.6344	Remote Similarity	NPD5363	Approved
0.6344	Remote Similarity	NPD5329	Approved
0.6344	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7331	Phase 2
0.6292	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6079	Approved
0.6286	Remote Similarity	NPD5697	Approved
0.6286	Remote Similarity	NPD5701	Approved
0.6277	Remote Similarity	NPD5280	Approved
0.6277	Remote Similarity	NPD4690	Approved
0.6277	Remote Similarity	NPD4693	Phase 3
0.6277	Remote Similarity	NPD5205	Approved
0.6277	Remote Similarity	NPD4138	Approved
0.6277	Remote Similarity	NPD4694	Approved
0.6277	Remote Similarity	NPD4689	Approved
0.6277	Remote Similarity	NPD5690	Phase 2
0.6277	Remote Similarity	NPD4688	Approved
0.6262	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7320	Approved
0.6226	Remote Similarity	NPD6899	Approved
0.6226	Remote Similarity	NPD6011	Approved
0.6226	Remote Similarity	NPD6881	Approved
0.6224	Remote Similarity	NPD4202	Approved
0.622	Remote Similarity	NPD7341	Phase 2
0.6214	Remote Similarity	NPD7632	Discontinued
0.6207	Remote Similarity	NPD4058	Approved
0.6207	Remote Similarity	NPD4687	Approved
0.6207	Remote Similarity	NPD5733	Approved
0.6196	Remote Similarity	NPD4269	Approved
0.6196	Remote Similarity	NPD4270	Approved
0.618	Remote Similarity	NPD4756	Discovery
0.617	Remote Similarity	NPD1696	Phase 3
0.6168	Remote Similarity	NPD6373	Approved
0.6168	Remote Similarity	NPD6014	Approved
0.6168	Remote Similarity	NPD6012	Approved
0.6168	Remote Similarity	NPD6372	Approved
0.6168	Remote Similarity	NPD6013	Approved
0.6162	Remote Similarity	NPD5282	Discontinued
0.6154	Remote Similarity	NPD6052	Approved
0.6129	Remote Similarity	NPD7154	Phase 3
0.6122	Remote Similarity	NPD7637	Suspended
0.6111	Remote Similarity	NPD6883	Approved
0.6111	Remote Similarity	NPD7290	Approved
0.6111	Remote Similarity	NPD7102	Approved
0.6105	Remote Similarity	NPD5786	Approved
0.61	Remote Similarity	NPD4629	Approved
0.61	Remote Similarity	NPD5210	Approved
0.6087	Remote Similarity	NPD5369	Approved
0.6055	Remote Similarity	NPD6649	Approved
0.6055	Remote Similarity	NPD6869	Approved
0.6055	Remote Similarity	NPD6847	Approved
0.6055	Remote Similarity	NPD6650	Approved
0.6055	Remote Similarity	NPD6617	Approved
0.6055	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8130	Phase 1
0.604	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7614	Phase 1
0.604	Remote Similarity	NPD4697	Phase 3
0.604	Remote Similarity	NPD5221	Approved
0.604	Remote Similarity	NPD5222	Approved
0.602	Remote Similarity	NPD4096	Approved
0.6019	Remote Similarity	NPD6404	Discontinued
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD8297	Approved
0.6	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6614	Approved
0.5981	Remote Similarity	NPD6412	Phase 2
0.5981	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4755	Approved
0.598	Remote Similarity	NPD5173	Approved
0.5978	Remote Similarity	NPD4252	Approved
0.5977	Remote Similarity	NPD5777	Approved
0.5957	Remote Similarity	NPD5362	Discontinued
0.5952	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7094	Approved
0.5946	Remote Similarity	NPD6858	Approved
0.5917	Remote Similarity	NPD7319	Approved
0.5914	Remote Similarity	NPD4139	Approved
0.5914	Remote Similarity	NPD4692	Approved
0.5913	Remote Similarity	NPD6319	Approved
0.5905	Remote Similarity	NPD5211	Phase 2
0.59	Remote Similarity	NPD5133	Approved
0.5875	Remote Similarity	NPD287	Approved
0.587	Remote Similarity	NPD4195	Approved
0.5865	Remote Similarity	NPD4700	Approved
0.5865	Remote Similarity	NPD5286	Approved
0.5865	Remote Similarity	NPD4696	Approved
0.5865	Remote Similarity	NPD5285	Approved
0.5854	Remote Similarity	NPD4193	Approved
0.5854	Remote Similarity	NPD4191	Approved
0.5854	Remote Similarity	NPD4194	Approved
0.5854	Remote Similarity	NPD4192	Approved
0.5851	Remote Similarity	NPD6435	Approved
0.5841	Remote Similarity	NPD6274	Approved
0.5841	Remote Similarity	NPD6868	Approved
0.5833	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD2067	Discontinued
0.5816	Remote Similarity	NPD4518	Approved
0.5812	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5223	Approved
0.5806	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4632	Approved
0.58	Remote Similarity	NPD7983	Approved
0.58	Remote Similarity	NPD8034	Phase 2
0.58	Remote Similarity	NPD8035	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data